HCID 68691509, compound → HCID 57918939, compound

HRID 2266256Notes

Reaction equation

HRID 2266256 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]=[C:8]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1)[C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1)[C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68691509HCID 68691509, compound

Product 1

HCID 57918939HCID 57918939, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 3-(4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)but-1-enyl)piperidine-1-carboxylate (110 mg, 0.85 mmol) in anhydrous MeOH (3 mL) was added anhydrous Pd(OH)2 (20 mg). The reaction mixture was stirred overnight under a hydrogen atmosphere (monitored by LC-MS) and filtered through a plug of silica. The filtrate was concentrated in vacuo to afford a mixture with two isomers. Purification by preparative HPLC gave (S)-tert-butyl 3-((R)-4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)butyl)piperidine-1-carboxylate (40 mg, 36% yield). 1H NMR (400 MHz, MeOH):7.31-7.37 (m, 2 H), 7.20 (d, 2 H), 7.13 (d, 2 H), 6.97-7.01 (m, 3 H), 3.95-4.18 (m, 1 H), 3.80-3.92 (m, 1 H), 3.03 (m, 2 H), 2.61-2.72 (m, 1 H), 2.42-2.52 (m, 1 H), 2.38 (d, 3 H), 1.90 (s, 3 H), 1.78 (m, 1 H), 1.42-1.65 (m, 4 H), 1.43 (s, 9 H), 1.15-1.31 (m, 3 H), 1.03 (m, 1 H). MS (E/Z): 483 (M+H+)

Workup

  1. filtrationfiltered through a plug of silica
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto afford a mixture with two isomers
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-6b1a4006a93549a68871622f8b84c9ff
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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